WO1996004237A1 - Procede de production de 0-(2-hydroxyalkyl)-oximes - Google Patents

Procede de production de 0-(2-hydroxyalkyl)-oximes Download PDF

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Publication number
WO1996004237A1
WO1996004237A1 PCT/EP1995/002932 EP9502932W WO9604237A1 WO 1996004237 A1 WO1996004237 A1 WO 1996004237A1 EP 9502932 W EP9502932 W EP 9502932W WO 9604237 A1 WO9604237 A1 WO 9604237A1
Authority
WO
WIPO (PCT)
Prior art keywords
oximes
hydroxyalkyl
oxime
epoxyalkyl
general formula
Prior art date
Application number
PCT/EP1995/002932
Other languages
German (de)
English (en)
Inventor
Albrecht Harreus
Norbert Götz
Harald Rang
Original Assignee
Basf Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to EP95927718A priority Critical patent/EP0775106B1/fr
Priority to US08/776,579 priority patent/US5739400A/en
Priority to BR9508494A priority patent/BR9508494A/pt
Priority to AU31654/95A priority patent/AU3165495A/en
Priority to MX9700808A priority patent/MX9700808A/es
Priority to JP8506156A priority patent/JPH10506380A/ja
Priority to CA002196451A priority patent/CA2196451C/fr
Priority to DE59504921T priority patent/DE59504921D1/de
Publication of WO1996004237A1 publication Critical patent/WO1996004237A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
    • C07C251/54—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
    • C07C249/12—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reactions not involving the formation of oxyimino groups

Definitions

  • the present invention relates to a process for the preparation of 0- (2-hydroxyalkyl) oximes of the general formula I.
  • R 1 and R 2 each represent al yl groups having 1 to 10 carbon atoms or are linked together with the carbon atom which bears them to form a 5- to 7-membered cycloalkyl radical.
  • 0- (2-hydroxyalkyl) oximes are of great importance as intermediates for crop protection agents (see, for example, the older German application DE-A 44 15 887).
  • the object of the invention was therefore to provide a process which leads to the 0- (2-hydroxyalkyl) oximes I with high regioselectivity and largely without formation of by-products.
  • R 1 and R 2 each represent a C 1 -C 6 -alkyl group and in particular a C 1 -C 4 -alkyl group, or together with the carbon atom, the it bears, form a cyclopentyl or cyclohexyl ring.
  • R 1 and R 2 each particularly preferably stand for methyl or ethyl, in particular both for methyl.
  • the 0- (2,3-epoxyalkyl) oximes II are generally known or can be obtained by known methods, especially by base-catalyzed reaction of the corresponding epihalohydrins with the free oximes in a dipolar aprotic solvent (see, for example, Zh. Org. Khim. ü, pages 1353 to 1355 (1969)).
  • Suitable catalysts for the hydrogenation are generally customary catalysts, such as those e.g. in "Houben-Weyl", Volume 4 / lc.
  • Preferred hydrogenation catalysts are those which contain a metal from groups 8 to 10 according to the IUPAC classification of the periodic system, preferably from the group of the elements cobalt, ruthenium, rhodium, especially from the group of the elements platinum and nickel and in particular palladium .
  • the catalysts can be used as such or preferably on a support.
  • Usual carrier materials such as silicon dioxide, aluminum oxide, titanium dioxide, silicates and zeolites and especially activated carbon come into consideration.
  • Binders or molding aids can also be used to produce the supported catalysts.
  • the catalysts can be used in the form of grit, strands, tablets or spheres.
  • Per mole of the compound II to be hydrogenated 0.1 to 2, preferably 0.1 to 1,% by weight of catalyst are generally used, this quantity being based on the active mass of the catalyst without support materials.
  • the hydrogenation can be carried out continuously or preferably discontinuously. When it is carried out batchwise in the liquid phase, the hydrogenation can be carried out in the presence of a solvent.
  • Polar solvents such as ethers and alcohols and mixtures thereof are suitable.
  • Preferred are ethers or alcohols with up to six carbon atoms such as 1,2-dimethoxyethane, ethanol, n-propanol, iso-propanol and n-butanol.
  • the pressure can be selected within wide limits, which range from 1 to 400 bar, but one preferably works in a pressure range from 1 to 100, especially from 10 to 70 and in particular from 30 to 50 bar.
  • the temperature in the hydrogenation is preferably 0 to 100, especially 10 to 50 and in particular 25 to 30 ° C.
  • reaction products I are isolated by methods known per se, preferably by distillation.
  • the yield of the compounds I are normally 70 to 90%, with a selectivity of generally more than 98%.
  • the 0- (2-hydroxyalkyl) oximes I obtainable by the process according to the invention are suitable as precursors for herbicides, in particular of the cyclohexenone type (cf. e.g. DE-A 44 15 887).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Medicinal Preparation (AREA)
  • Steroid Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne un procédé de production de 0-(2-hydroxyalkyl)-oximes de formule (I) où R1 et R2 représentent alkyle, ou bien R1 et R2 ainsi que l'atome de carbone qui les porte représentent un cycloalkyle de cinq à sept chaînons. Ce procédé consiste à hydrogéner par voie catalytique un 0-(2,3-époxyalkyl)-oxime de formule (II). Les produits de formule (I) se prêtent à une utilisation sous forme d'intermédiaires pour herbicides.
PCT/EP1995/002932 1994-08-02 1995-07-25 Procede de production de 0-(2-hydroxyalkyl)-oximes WO1996004237A1 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
EP95927718A EP0775106B1 (fr) 1994-08-02 1995-07-25 Procede de production de 0-(2-hydroxyalkyl)-oximes
US08/776,579 US5739400A (en) 1994-08-02 1995-07-25 Preparation of O-(2-hydroxyalkyl)oximes
BR9508494A BR9508494A (pt) 1994-08-02 1995-07-25 Processo para a preparação de oximas de o-(2-hidroxialquila)
AU31654/95A AU3165495A (en) 1994-08-02 1995-07-25 Method of producing o-(2-hydroxyalkyl)-oximes
MX9700808A MX9700808A (es) 1994-08-02 1995-07-25 Metodo para la produccion de o-(2-hidroxialquil)-oximas.
JP8506156A JPH10506380A (ja) 1994-08-02 1995-07-25 Ｏ−（２−ヒドロキシアルキル）オキシムの製造方法
CA002196451A CA2196451C (fr) 1994-08-02 1995-07-25 Procede de production de 0-(2-hydroxyalkyl)-oximes
DE59504921T DE59504921D1 (de) 1994-08-02 1995-07-25 Verfahren zur herstellung von o-(2-hydroxyalkyl)-oximen

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4427290A DE4427290A1 (de) 1994-08-02 1994-08-02 Verfahren zur Herstellung von O-(2-Hydroxyalkyl)-oximen
DEP4427290.1 1994-08-02

Publications (1)

Publication Number Publication Date
WO1996004237A1 true WO1996004237A1 (fr) 1996-02-15

Family

ID=6524700

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/002932 WO1996004237A1 (fr) 1994-08-02 1995-07-25 Procede de production de 0-(2-hydroxyalkyl)-oximes

Country Status (17)

Country Link
US (1) US5739400A (fr)
EP (1) EP0775106B1 (fr)
JP (1) JPH10506380A (fr)
KR (1) KR100388881B1 (fr)
CN (1) CN1046705C (fr)
AT (1) ATE175956T1 (fr)
AU (1) AU3165495A (fr)
BR (1) BR9508494A (fr)
CA (1) CA2196451C (fr)
DE (2) DE4427290A1 (fr)
ES (1) ES2126920T3 (fr)
HU (1) HU215284B (fr)
IL (1) IL114798A (fr)
MX (1) MX9700808A (fr)
MY (1) MY114890A (fr)
WO (1) WO1996004237A1 (fr)
ZA (1) ZA956401B (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2325626A1 (fr) * 1975-09-23 1977-04-22 Union Carbide Corp Procede de preparation de 2-phenylethanol
EP0023560A1 (fr) * 1979-07-05 1981-02-11 BASF Aktiengesellschaft Procédé de préparation de cétoximes substitués sur l'atome d'oxygène
DE4415887A1 (de) * 1994-05-05 1995-06-01 Basf Ag Verfahren zur Herstellung von O-Phenoxyalkyloximen und O-Phenoxyalkylhydroxylaminen

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3040097A (en) * 1959-04-06 1962-06-19 Purdue Research Foundation Beta-hydroxy alkyl ethers of oximes and production thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2325626A1 (fr) * 1975-09-23 1977-04-22 Union Carbide Corp Procede de preparation de 2-phenylethanol
EP0023560A1 (fr) * 1979-07-05 1981-02-11 BASF Aktiengesellschaft Procédé de préparation de cétoximes substitués sur l'atome d'oxygène
DE4415887A1 (de) * 1994-05-05 1995-06-01 Basf Ag Verfahren zur Herstellung von O-Phenoxyalkyloximen und O-Phenoxyalkylhydroxylaminen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
M. BOUZOUBAA ET. AL.: "Synthesis and beta-Adrenergic Blocking Activity of New Aliphatic and alicyclic Oxime Ethers.", JOURNAL OF MEDICINAL CHEMISTRY, vol. 27, no. 10, October 1984 (1984-10-01), WASHINGTON US, pages 1291 - 4 *

Also Published As

Publication number Publication date
BR9508494A (pt) 1999-06-01
ZA956401B (en) 1997-02-03
HU215284B (hu) 1998-11-30
ATE175956T1 (de) 1999-02-15
KR100388881B1 (ko) 2004-07-16
EP0775106B1 (fr) 1999-01-20
IL114798A (en) 1999-10-28
JPH10506380A (ja) 1998-06-23
ES2126920T3 (es) 1999-04-01
MX9700808A (es) 1997-05-31
CN1046705C (zh) 1999-11-24
MY114890A (en) 2003-02-28
DE59504921D1 (de) 1999-03-04
CA2196451A1 (fr) 1996-02-15
AU3165495A (en) 1996-03-04
HUT77513A (hu) 1998-05-28
IL114798A0 (en) 1995-12-08
US5739400A (en) 1998-04-14
KR970704670A (ko) 1997-09-06
CN1156444A (zh) 1997-08-06
DE4427290A1 (de) 1996-02-08
CA2196451C (fr) 2005-09-06
EP0775106A1 (fr) 1997-05-28

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